“I can tell if a podcast is going to stink beforehand if the person has a PR person asking for questions.” Digiday’s Brian Morrissey on Digital Media, VC and Light at the End of the Tunnel.

Twitter Friend. Digiday’sBrian Morrissey is a Twitter Friend. That is, we’ve never met IRL but through his tweets, his podcast and our occasional DMs, he feels, well, familiar. So I decided to ask him Five Questions and get to know Brian a bit better.

Hunter Walk: What’s Digiday and how’d you end up there?

Brian Morrissey:Digiday is a media brand focused on the changing nature of the media and marketing businesses as they collide with digital technology. I joined Digiday seven years ago after many years reporting on the industry. At the time, Digiday was mostly an events-focused company. The idea was to build a publishing-focused brand with events as a revenue base while we figured out our own differentiation in a crowded market — and then added business lines around advertising, custom content and now subscriptions.

We’ve since expanded under Digiday Media to have other brands. Glossy focuses on the changing nature of the fashion and beauty industries as they collide with digital technology, new business models, and the need for sustainability and inclusivity. Tearsheet is our publication focused on the changing nature of payments and financial services. All three brands are built around offering a differentiated point of view, establishing direct connections with the audience, and making money in a variety of ways. One of the best things about Digiday is we not only cover the search for sustainable media but we live it ourselves as an independent media company without VC money. We’re about 80 people now, in NYC and London mostly, and profitable.

HW: Your Digiday podcast is one of my favorite in the media industry. I especially appreciate that you’re direct without being confrontational just for the sake of it. Can you tell within the first few minutes of recording whether it’s going to be a good discussion or not? Is there a guest or two that you especially enjoy jousting with?

BM: I always found as a reporter that the best interviews I did were outside the office over coffee. Being a reporter is about putting people at ease somewhat to find out information and something approximating the truth. So much of what people say as business executives is PR. I can tell if a podcast is going to stink beforehand if the person has a PR person asking for questions. That’s a red flag. The thing I like about with podcasts is you can’t repeat talking points for a half hour. It sounds ridiculous.

The best interviews are people I know well because they won’t take any probing personally. Some favorites: GroupNine’s Ben Lerer, Hearst’s Troy Young, Complex’s Rich Antoniello, Cheddar’s Jon Steinberg, Barstool’s Erika Nardini. I’d also include journalists since there’s an easier rapport there and allergy to bullshit: Some favorites: Wired’s Nick Thompson, The Information’s Jessica Lessin, Recode’s Kara Swisher.

HW: Homebrew, my venture fund, is an investor in several “media” platforms (such as Anchor, Cheddar and theSkimm) but I tend to think venture dollars can really mess up a media company if raised too early or too abundantly. How should media entrepreneurs weigh funding options for their startups?

BM: I hate when people answer my questions with “it depends,” but I’m going to do that here. We’ve built Digiday without venture capital. Nick Friese founded it a decade ago with savings and early 401(k) withdrawals. We have funded ourselves over the years with an exotic formula of bringing in more money than we spend. The upsides to this is you can make quicker decisions and constraints keep you from doing dumb stuff like pivoting to video. The downsides are you skimp on infrastructure and can be at risk of not being aggressive enough in meeting opportunities because you don’t want to get too far ahead of revenue.

VCs always stayed away from media models for scale reasons. The period of scale media models being attractive for VC is probably over now that Google and Facebook have vacuumed up most of the digital ad market. Too many people seem to take VC money based on that Mary Meeker slide that showed the delta between time spent on the Internet and budgets spent. Well, that delta is gone, but the money mostly went to Google and Facebook.

There are some very significant media businesses being built that couldn’t have been done without VC. But right now, I’d say the most attractive media models are ones with close ties to their audiences rather than mass scale plays. Not to talk up your book but that’s what I find interesting about theSkimm, which has a direct connection with an audience and a real brand differentiation. (Jon will be mad if I don’t mention Cheddar too. So I find Cheddar interesting.)

HW: What are some other digital media businesses you admire?

BM: My favorite media businesses tend to be those focused on an obsessive audience, coupled with a balanced business model. For Digiday, we gravitate to the business side because people ideally are obsessed about their livelihoods, but industries like media, marketing, fashion and beauty have a bigger cultural impact that attracts people from both adjacent industries and those simply into these areas. A lot of people still call this “trade,” but I don’t see it that way. Trade was synonymous with being boring and cheerleaders. There’s an opportunity and need to take a different approach as people’s work and personal lives blur.

On the consumer side, I like what companies like Hypebeast and Highsnobiety are doing, having started as streetwear blogs and now growing into lifestyle media brands. Focused brands like Hodinkee, which is all about high-end watches, interest me because the audience is obsessive. I’m impressed by Axios in the impact it has made in such a short time, even if I’d like it to stop telling me to “be smarter.” We’re coming out of an era of flimsy media models built off ephemeral, manufactured audiences that were from platforms. The media models that are best positioned now have tight connections with defined communities — and strong, differentiated brands.

HW: What’s a contrarian take that you hold about the nearterm future of digital media?

BM: My contrarian take is that underneath all the gloom and unrelenting pressure on media that there are several hopeful signs of sustainability coming to media models. Yes, the duopoly. But the pivot to paid is promising. Just a few years ago it was thought impossible for paid models to work for digital media. We’re seeing that not necessarily be the case on the very high end consumer side (NYT, WaPo), the vertical B2B (The Information, Digiday) and focused consumer (theSkimm, The Athletic). Digital media went pear shaped when it fell in love with scale and ads. You need diversity in revenue streams. There are other models emerging off media outside of news, such as Clique Media, Glossier, Goop, Barstool.

On top of that, I think the platforms getting beat up over Russian trolls, data leaks, crushing media, etc will help align interests better. Facebook and Google will need to give a lot more to media right now. I can’t think of a time when publishers had more leverage. And many of the impacts of GDPR and laws like it are still unknown, but I think these efforts to rein in data promiscuity will combine with an inevitable swing back to context over specific audience to help publishers in the long run. How long, I’m not sure. But I’m optimistic for the future of our own business. We keep growing and see a ton of opportunities to go both deeper (new services, revenue lines with subs) and wider (new geographies, brands). The challenges are all real; I don’t think they’re insurmountable.